Patent GB-466344-A (GB)
Title: Improvements in the manufacture and production of nitrogenous products
IPC: C08G73/02
Filed: 1935-08-22
Abstract: Assistants useful in the textile, leather, lacquer, rubber, pharmaceutical, and cosmetic industries are obtained when mono or polymeric 1 : 2-alkyleneimines are condensed with aliphatic alcohols or oxides or esters thereof, other than carboxylic acid esters.  The treatment of monomeric ethyleneimine or N-methylethyleneimine with methyliodide is also excluded.  The reaction may be combined with a condensation with (a) aldehydes and ketones, (cf. Specification 466,346); (b) halogenated aromatic compounds and aromatic sulphonic halides, (cf. Specification 466,345), or (c) other substances capable of condensation, e.g. urea or its substitution products such as dimethylolurea, thiourea, phenols, cetylamine, octodecylamine or other amine or styrene, synthetic rubber or synthetic resins.  The condensation may be effected in the presence of solvents or diluents such as water, alcohol, ether, cyclohexanone, toluene, carbontetrachloride or chlorbenzene.  Acyl, sulphonic, sulphuric ester, carboxylic or phosphoric acid groups may be introduced into the products or into the reacting components.  The products may be added in dyeing, printing, dressing, stripping, fulling, levelling, tanning, washing, dispersing and wetting processes. They may also be used in softening and flotation agents and to increase the affinity of viscose or copper artificial silk for acid dyestuffs.  They may be added to spinning solutions and the products obtained with the co-employment of aldehydes or ketones may be used for dressing textiles, leather, paper or straw and for rendering artificial silk crease and slide proof.  Dispersing agents such as sulphuric esters of fatty alcohols and aliphatic sulphonic acids may be used with the products, which can also be employed in the form of salts with mineral or organic, e.g. fatty acids.  In examples: (1) polymerized ethyleneimine is treated with the alkyl bromides corresponding to palm kernel fatty acids; the products may be treated with chlorsulphonic acid or phosphorus oxychloride to render them soluble; a textile fabric is treated with a solution of the product in a solvent and then passed into a bath of formaldehyde: a resin is produced by treating the product with excess formaldehyde; (2) polymerized ethyleneimine or its reaction product with b  : b <1>-dichlordiethylether is reacted with stearylisocyanate; the reaction may be carried out on a textile fibre; the product may be treated with chlorethanesulphonic acid or chlorsulphonic acid; (3) ethyleneimine is reacted with benzylchloride or the alkylbromides derived from palm kernel oil and the product treated with ethyleneoxide; (4) propylethyleneimine is reacted with epichlorhydrin; the product is a preservative against moths; (5) polymerized ethyleneimine is treated with a chlorinated paraffin wax; the product may be reacted with benzylchloride, dimethylsulphate; or ethyleneoxide to obtain further products which may be added to viscose or copper artificial silk spinning solutions; (6) polymeric C-butyleneimine is treated with sodium chlorethanesulphonate; and the product condensed with butyl, hexyl, octodecenyl chloride or octodecyl bromide; (7) polymeric propyl or phenylethyleneimine is reacted with monoglycerol chlorhydrin; by introducing high molecular aliphatic radicles, e.g. by means of dodecyl bromide, products having a water repelling action are obtained; (8) polymeric butyl, hexyl or dodecylethyleneimine is treated with ethylene or propylene oxide, or glycide; (9) N-phenyl, benzyl or cyclohexylethyleneimine is treated with ethylene oxide to obtain a levelling agent having disinfecting action; (10) ethyl or butyl ethyleneimine is reacted with ethyleneoxide to obtain a product suitable for adding to viscose and copper artificial silk spinning baths; (11) polymeric ethyleneimine is treated first with ethylene oxide and then with sodium benzyl chloride sulphonate.  Methylethyleneimine and o -chlor-a  : b -butyleneimine are specified and the use of dichloroctodecane and butylene oxide is mentioned.ALSO:Products which may be added to preparations used as dispersing agents are obtained when mono or polymeric 1 : 2-alkyleneimines are condensed with aliphatic alcohols or oxides or esters thereof--other than carboxylic acid esters.  The treatment of monomeric ethyleneimine of N-methylethyleneimine with methyliodide is also excluded.  The reaction may be combined with a condensation with (a) aldehydes and ketones, cf. Specification 466,346, (b) halogenated aromatic compounds and aromatic sulphonic halides, cf. Specification 466,345, or (c) other substances capable of condensation, e.g. urea or its substitution products such as dimethylolurea, thiourea, phenols, cetylamine, octodecylamine or other amine or styrene, synthetic rubber or synthetic resins.  Acyl, sulphonic, sulphuric ester, carboxylic, or phosphonic acid groups may be introduced into the products or into the reacting components. Dispersing agents such as sulphuric esters of fatty alcohols and aliphatic sulphonic acids may be used with the products, which can also be employed in the form of salts with mineral or organic, e.g. fatty acids.  In examples: (1) polymerized ethyleneimine is treated with the alkyl bromides corresponding to palm kernel fatty acids; the products may be treated with chlorsulphonic acid or phosphorus oxychloride to render them soluble; a resin is produced by heating the product with excess formaldehyde; (2) polymerized ethyleneimine or its reaction product with b  : b -dichlordiethylether is reacted with stearylisocyanate; the product may be treated with chlorethanesulphonic acid or chlorsulphonic acid; (3) ethyleneimine is reacted with benzylchloride or the alkylbromides derived from palm kernel oil and the product treated with ethyleneoxide; (4) propylethyleneimine is reacted with epichlorhydrin; (5) polymerized ethyleneimine is treated with a chlorinated paraffin wax; the product may be reacted with benzylchloride, dimethylsulphate or ethyleneoxide to obtain further products; (6) polymeric C-butyleneethyleneimine is treated with sodium chlorethanesulphonate; and the product condensed with butyl, hexyl or octodecenyl chloride or octodecyl bromide; (7) polymeric propyl or phenylethyleneimine is reacted with monoglycerol chlorhydrin; by introducing high molecular aliphatic radicles, e.g. by means of dodecyl bromide, further products are obtained; (8) polymeric butyl, hexyl or dodecyl ethyleneimine is treated with ethylene or propylene oxide or glycide; (9) N-phenyl, benzyl or cyclohexylethyleneimine is treated with ethylene oxide; (10) ethyl or butyl ethyleneimine is reacted with ethyleneoxide; (11) polymeric ethyleneimine is treated first with ethylene oxide and then with sodium benzyl chloride suphonate. Methylethyleneimine and o -chlor-a : b -butyleneimine are specified, and the use of dichloroctodecane and butylene oxide is mentioned.